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[ CAS No. 904326-88-1 ]

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Chemical Structure| 904326-88-1
Chemical Structure| 904326-88-1
Structure of 904326-88-1 * Storage: {[proInfo.prStorage]}

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Product Details of [ 904326-88-1 ]

CAS No. :904326-88-1 MDL No. :MFCD11878345
Formula : C11H18BN3O2 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W :235.09 g/mol Pubchem ID :-
Synonyms :

Safety of [ 904326-88-1 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P264-P271-P280-P302+P352-P304+P340+P312-P305+P351+P338-P332+P313-P337+P313-P362-P403+P233-P405-P501 UN#:
Hazard Statements:H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 904326-88-1 ]

  • Downstream synthetic route of [ 904326-88-1 ]

[ 904326-88-1 ] Synthesis Path-Downstream   1~15

YieldReaction ConditionsOperation in experiment
50%
50% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane at 85℃; Inert atmosphere; 39.39b Step 34b: N-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetamide (Compound 0602-107) General procedure: Step 34b: N-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetamide (Compound 0602-107)[0334]To a solution of compound 0601-107 (2.5 g, 11.6 mmol) and bis(pinacolato)diboron (4.4 g, 17.5 mmol) in dioxane (100 mL) was added potassium acetate (3.4 g, 35 mmol) and PdCl2(dppf)2 (0.95 g, 1.1 mmol). The mixture was degassed with nitrogen and heated at 85° C. for overnight. The reaction mixture was concentrated under reduced pressure to afford the crude product, which purified by column chromatography (ethyl acetate in petroleum ether, 15% v/v) to give the compound 0602-107 (1.55 g, 51%) as a pink solid. LCMS: 262 [M+1]+. 1H NMR (400 MHz, DMSO-d6) δ 1.29 (s, 12H), 2.03 (s, 3H), 7.30 (s, 1H), 7.31 (d, J=2.0 Hz 1H), 7.73 (d, J=2.0 Hz, 1H), 7.89 (d, J=1.6 Hz, 1H), 9.93 (s, 1H).
50% With palladium bis[bis(diphenylphosphino)ferrocene] dichloride; potassium acetate In 1,4-dioxane at 85℃; Inert atmosphere; 39b N-(3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl) acetamide (Compound 0602-107) General procedure: Compound in dioxane (100mL) 0601-107 (2.5g, 11.6mmol) and a solution of bis (pinacolato) diboron (4.4 g, 17.5 mmol), potassium acetate (3.4 g, 35 mmol) and and PdCl2 (dppf) 2 ( 0.95g, 1.1mmol) was added. The mixture was degassed with nitrogen and heated overnight at 85 ° C.. The reaction mixture was concentrated under reduced pressure to give the crude product, which was purified by column chromatography (petroleum ether in ethyl acetate, 15% v / v) to give the compound 0602-107 as a pink solid obtained (1.55 g, 51%).
  • 2
  • [ 31402-54-7 ]
  • [ 73183-34-3 ]
  • [ 904326-88-1 ]
YieldReaction ConditionsOperation in experiment
100% With potassium acetate In N,N-dimethyl-formamide at 80℃; for 2h; Inert atmosphere; 18.2 N,N-Dimethylformamide (20 ml) was added to 5-bromo-N-methylpyrimidin-2-amine (3.0 g, 16.0 mmol), bispinacolatodiboron (4.86 g, 19.2 mmol), and potassium acetate (4.7 g, 47.9 mmol) and the atmosphere in the reaction vessel was substituted with nitrogen. A 1,1'-bis(diphenylphosphino)ferrocene]palladium (II) dichloride dichloromethane complex (650 mg, 0.80 mmol) was added, the atmosphere in the reaction vessel was substituted with nitrogen again, and the resulting mixture was stirred at 80° C. for 2 hours. The reaction mixture was partitioned with ethyl acetate and saturated brine and filtrated through celite and the organic layer was washed twice with saturated brine and dried over magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel chromatography (hexane:ethyl acetate=8:2 to 6:4) to give the title compound (3.8 g, 100%) as a white solid.1H-NMR (CDCl3) δ: 1.32 (12H, s), 3.03 (3H, d, J=5.12 Hz), 5.66 (1H, brs), 8.58 (2H, brs).
82% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane at 115℃; for 5h; Inert atmosphere; 20 /V-methyl-5-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)pyrimidin-2-amine (i 12): /V-methyl-5-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)pyrimidin-2-amine (i 12): To a stirred solution of 5-bromo-/V-methylpyrimidin-2-amine (0.5 g, 2.65 mmol) in dioxane (10 ml_), bispinacolatodiboron (0.81 g, 3.19 mmol) and KOAc (0.39 g, 3.97 mmol) were added and the reaction was degassed with argon for 20 min. PdCI2(dppf) (0.19 g, 0.26 mmol) was then added and the reaction mixture was purged with argon for another 10 min. The reaction was heated at 1 15°C for 5h. The progress of the reaction was monitored by TLC. After completion, the reaction mixture was diluted with ethyl acetate, filtered and filtrate was concentrated under reduced pressure to afford /V-methyl-5-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)pyrimidin-2- amine (i12) (0.5 g, 82%). MS (ESI) m/e (M+1 )+: 236
64% With potassium acetate In 1,4-dioxane at 115℃; for 4.25h; Heating / reflux; 2 [0240] To a dry 50O mL flask was added 2-methylamino-5-bromopyrimidlne(9.5 g, 50.5 mmol), potassium acetate (15.1 g, 154.4 mmol), 4,4,5,5,-tetramethyl-2- (4,4,5,5,-tetramethyl-l,3,2-dioxaborolan-2-yl)-l,3,2-dioxaborolane (14.1 g, 55.5 mmol) and dioxane (280 mL). Argon was bubbled through the solution for 15 minutes, at which time l,l'-bis(diphenylphosphino)ferrocene palladium(H) chloride dichloromethane adduct (2.05 g, 2.51 mmol) was added. The reaction was refluxed in a 115 0C oil bath for 4 hours under argon. After cooling to room temperature, EtOAc (500 mL) was added and the resulting slurry was sonicated and filtered. Additional EtOAc (500 mL) was used to wash the solid. The combined organics were washed with H2O (2x300 mL), NaCl(Saq, (300 mL), dried over Na2SO4, filtered and the solvents were removed in vacuo. Purification by SiO2 chromatography (50% EtOAc/hexanes) yielded an off white solid (7.66 g, 64%). LCMS (m/z): 154 (MH+ of boronic acid, deriving from in situ product hydrolysis on LC). 1H NMR (CDCl3): δ 8.58 (s, 2H), 5.56 (s, IH), 3.02 (d, 3H), 1.32 (s, 12H).
64% With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In 1,4-dioxane at 115℃; for 4h; Inert atmosphere;
64% With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In 1,4-dioxane at 115℃; for 4h; Inert atmosphere; 2 Synthesis of methyl[5-(4,4,5,5-tetramethyl(l ,3,2-dioxaborolan-2-yl))pyrimidin-2- yl] amine[0085] To a dry 500 mL flask was added 2-methylamino-5-bromopyrimidine (9.5 g, 50.5 mmol), potassium acetate (15.1 g, 154.4 mmol), 4,4,5,5, -tetramethyl-2-(4,4,5, 5,- tetramethyl-l ,3,2-dioxaborolan-2-yl)-l,3,2-dioxaborolane (14.1 g, 55.5 mmol) and dioxane (280 mL). Argon was bubbled through the solution for 15 minutes, at which time l,l'-bis(diphenylphosphino)ferrocene palladium(II) chloride dichloromethane adduct (2.05 g, 2.51 mmol) was added. The reaction was refluxed in a 1 15 °C oil bath for 4 hours under argon. After cooling to room temperature, EtOAc (500 mL) was added and the resulting slurry was sonicated and filtered. Additional EtOAc (500 mL) was used to wash the solid. The combined organics were washed with H20 (2x300 mL), NaCl(sat ), (300 mL), dried over Na2S04, filtered and the solvents were removed in vacuo. Purification by Si02 chromatography (50% EtOAc/hexanes) yielded an off white solid (7.66 g, 64%).LCMS (m/z): 154 (MH+ of boronic acid, deriving from in situ product hydrolysis on LC). ¾ NMR (CDCls): δ 8.58 (s, 2H), 5.56 (s, 1H), 3.02 (d, 3H), 1.32 (s, 12H).

  • 3
  • [ 904326-88-1 ]
  • [ 1222105-32-9 ]
  • [ 1222105-72-7 ]
YieldReaction ConditionsOperation in experiment
61% With sodium carbonate In 1,4-dioxane; water at 20℃; for 3.5h; Reflux; Inert atmosphere; 16.1 Sodium carbonate (2.40 g, 22.7 mmol) and tetrakis triphenylphosphine palladium (0.44 g, 0.38 mmol) were added to a 1,4-dioxane (44.0 ml)-water (22.0 ml) mixture solution of 2-chloro-9-(cyclopropylmethyl)-6-morpholin-4-yl-9H-purine (2.22 g, 7.56 mmol) and 2-methylaminopyrimidine-5-boronic acid pinacol ester (2.31 g, 9.82 mmol) at room temperature and the resulting mixture was heated to reflux for 3.5 hours in an argon atmosphere. The reaction mixture was left standing to cool and then poured into water and ethyl acetate was added to separate the layers. The solid precipitated in the aqueous layer was collected by filtration, washed with water, and then dried at 50° C. under reduced pressure. Meanwhile, the organic layer was dried over anhydrous sodium sulfate, the mixture was filtrated, then the filtrate was concentrated under reduced pressure, and the resulting solid was washed with dichloromethane and collected by filtration. These solids were combined to give the title compound (1.68 g, 61%) as a white solid.1H-NMR (CDCl3) δ: 0.47-0.52 (2H, m), 0.63-0.69 (2H, m), 1.28-1.37 (1H, m), 3.09 (3H, d, J=5.15 Hz), 3.84-3.88 (4H, m), 4.06 (2H, d, J=7.45 Hz), 4.27-4.45 (4H, brm), 5.24-5.34 (1H, m), 7.82 (1H, s), 9.29 (2H, s).
  • 4
  • [ 904326-88-1 ]
  • [ 1222105-38-5 ]
  • [ 1222105-82-9 ]
YieldReaction ConditionsOperation in experiment
41% With sodium carbonate In 1,4-dioxane; water for 3h; Inert atmosphere; Reflux; 18.3 1,4-Dioxane (40 ml), water (20 ml), and sodium carbonate (2 g, 19 mmol) were added to N-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidin-2-amine (1.45 g, 6.18 mmol) and 2-chloro-6-morpholin-4-yl-9-(tetrahydrofuran-3-ylmethyl)-9H-purine (2.0 g, 6.18 mmol) and the atmosphere in the reaction vessel was substituted with nitrogen. Tetrakis triphenylphosphine palladium (0.36 g, 0.31 mmol) was added, then the atmosphere in the reaction vessel was substituted with nitrogen again, and the resulting mixture was heated to reflux for 3 hours. The reaction mixture was partitioned with ethyl acetate and water, the organic layer was dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. Methylene chloride-ether was added to the residue and the insoluble matter was collected by filtration and dried to give the title compound (1.0 g, 41%) as a white solid.1H-NMR (CDCl3) δ: 1.71-1.78 (1H, m), 2.02-2.08 (1H, m), 2.95-2.99 (1H, m), 3.09 (3H, d, J=5.15 Hz), 3.66 (1H, dd, J=8.88, 4.87 Hz), 3.76-3.81 (2H, m), 3.85-3.87 (4H, m), 3.94-3.99 (1H, m), 4.17 (1H, dd, J=13.75, 8.02 Hz), 4.23 (1H, dd, J=14.03, 7.73 Hz), 4.35 (4H, s), 5.29-5.32 (1H, m), 7.70 (1H, s), 9.28 (2H, s).
  • 5
  • [ 904326-88-1 ]
  • [ 944401-95-0 ]
  • [ 1254697-44-3 ]
YieldReaction ConditionsOperation in experiment
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate In 1,2-dimethoxyethane; water at 120℃; for 0.166667h; Microwave irradiation;
  • 6
  • [ 904326-88-1 ]
  • [ 1369485-77-7 ]
  • [ 1369484-95-6 ]
YieldReaction ConditionsOperation in experiment
With sodium carbonate In tetrahydrofuran at 90℃; for 16h; 27 Method 27: Synthesis of {5-r5-((R)-l-Cvclopropyl-l-{5-ri-(tetrahvdro-pyran-4-yl)- lH-pyrazol^-yll^l^^loxadiazol-S-yll-ethv -pyridin^-yll-pyrimidin^-v -methyl- amine Example 169)1-36.5 R-30 Example 169To a pressure tube is added 1-36.5 (213 mg, 0.53 mmol), R-30 (150 mg, 0.64 mmol), Tetrakis(triphenylphosphine)palladium (0) (61 mg, 0.053 mmol) and 2M aq. Na2C03 (1 ml, 2 mmol) in THF (8 ml). The reaction mixture is stirred at 90 °C for 16 hours. The reaction mixture is conecntrated in vacuo. The residue is diluted with EtOAc, is washed with water, brine, is dried under anhy. Na2S04, and is filtered and concentrated. The residue is purified by flash chromatography (Si02, 0-5% MeOH/CH2Cl2) to afford the title compound (131 mg); m/z 473.4 [M+l]
  • 7
  • [ 904326-88-1 ]
  • [ 1339925-58-4 ]
  • [ 1339925-65-3 ]
YieldReaction ConditionsOperation in experiment
43% With bis-triphenylphosphine-palladium(II) chloride In ethanol; water; toluene at 90℃; for 3h; Inert atmosphere; 100.100a Step 100a: Ethyl 5-(tert-butoxycarbonyl(2-(2-(methylamino)pyrimidin-5-yl)-4-morpholinothieno[3,2-d]pyrimidin-6-yl)amino)pentanoate (Compound 1103-227) Step 100a: Ethyl 5-(tert-butoxycarbonyl(2-(2-(methylamino)pyrimidin-5-yl)-4-morpholinothieno[3,2-d]pyrimidin-6-yl)amino)pentanoate (Compound 1103-227)[0651]A mixture of 1102-226 (300 mg, 0.6 mmol), N-methyl-5-(4,4,5,5-tetra methyl-1,3,2-dioxaborolan-2-yl)pyrimidin-2-amine (0602-227) (645 mg, 4.22 mmol) and Pd(PPh3)2Cl2 (12.7 mg) in a mixed solvents of toluene (6 mL), ethanol (4 mL) and water (1 mL) was stirred at 90° C. for 3 h under N2 atmosphere. After the completion of the reaction (monitored by TLC), the reaction mixture was concentrated and the residue was purified by column chromatography eluted with methanol in dichloromethane to afford title product as a colorless oil (150 mg, 43%). 1HNMR (400 MHz, DMSO-d6): δ 1.16 (t, J=7.2 Hz, 3H), 1.53 (s, 9H), 1.60-1.80 (m, 4H), 2.36 (t, J=6.4 Hz, 2H), 2.87 (d, J=4.8 Hz, 3H), 3.78 (t, J=4.4 Hz, 4H), 3.90-3.96 (m, 6H), 4.04 (q, J=7.2 Hz, 2H), 6.99 (s, 1H), 7.52 (d, J=4.8 Hz, 1H), 9.14 (br, 2H).
  • 8
  • [ 904326-88-1 ]
  • [ 1476076-22-8 ]
  • C19H21N7O [ No CAS ]
YieldReaction ConditionsOperation in experiment
65% With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; palladium diacetate; sodium carbonate In water; isopropyl alcohol at 120℃; for 0.5h; Inert atmosphere; Microwave irradiation; 6.v Example 6 Preparation (S)-N-(2-(2,3-dihydrofuro[3,2-b]pyridin-7-yl)propyl)-6-(6-(methylamino)pyridin-3-yl)pyrimidin-4-amine (Compound 430) As shown in step 6-v of Scheme 6, (S)-6-chloro-N-(2-(2,3-dihydrofuro[3,2-b]pyridin-7-yl)propyl)pyrimidin-4-amine (29.2 mg, 0.1003 mmol), N-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine (30.7 mg, 0.2006 mmol), Na2CO3 (150.4 μL of 2 M aqueous solution, 0.3009 mmol), and i-PrOH (2.0 mL) were combined and flushed with nitrogen gas for 10 minutes. SPhos (water soluble, 10.28 mg, 0.0201 mmol) and Pd(OAc)2 (1.13 mg, 0.0050 mmol) were added and the reaction vessel sealed and heated to 120° C. in a microwave for 30 minutes. The reaction mixture was filtered over diatomaceous earth and the filtrate was concentrated under reduced pressure. The residue was purified by reversed-phase HPLC (0-30% CH3CN/H2O, 0.1% TFA). The TFA salt obtained was neutralized using a StratoShperes PL-HCO3 MP-Resin cartridge to provide (S)-N-(2-(2,3-dihydrofuro[3,2-b]pyridin-7-yl)propyl)-6-(6-(methylamino)pyridin-3-yl)pyrimidin-4-amine (Compound 430, 23.8 mg, 65% yield): LCMS=364.12 (M+H); 1H NMR (400 MHz, DMSO-d6) δ 8.83 (s, 2H), 8.41 (s, 1H), 7.90 (d, J=5.1 Hz, 1H), 7.55 (s, 1H), 7.39 (s, 1H), 7.01 (s, 1H), 6.77 (s, 1H), 4.61 (t, J=8.4 Hz, 2H), 3.66-3.40 (m, 2H), 3.26-3.12 (m, 3H), 2.86 (d, J=4.5 Hz, 3H), 1.21 (d, J=6.6 Hz, 3H).
  • 9
  • [ 904326-88-1 ]
  • (S)-6-chloro-N-[2-(2,3-dihydro-[1,4]dioxino[2,3-b]pyridin-8-yl)propyl]pyrimidin-4-amine [ No CAS ]
  • (S)-N6-(2-(2,3-dihydro-[1,4]dioxino[2,3-b]pyridin-8-yl)propyl)-N2'-methyl-[4,5'-bipyrimidine]-2',6-diamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate In isopropyl alcohol at 80℃; 7.vi Example 7 Preparation of (S)-N6-(2-(2,3-dihydro-[1,4]dioxino[2,3-b]pyridin-8-yl)propyl)-N2′-methyl-[4,5′-bipyrimidine]-2′,6-diamine (Compound 462) As shown in step 7-vi of Scheme 7,6-chloro-N-[2-(2,3-dihydro-[1,4]dioxino[2,3-b]pyridin-8-yl)propyl]pyrimidin-4-amine (410 mg) was dissolved in IPA (0.75 mL). N-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidin-2-amine (23 mg) was added, followed by the addition of 2M Na2CO3 (122 μL) and 1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II), dichloromethane complex (7 mg). The reaction vessel was sealed and heated at 80° C. overnight. The mixture was cooled, diluted with ethyl acetate, washed with water, dried over Na2SO4, filtered, concentrated under reduced pressure and purified by reversed-phase HPLC, 5-50% ACN/H2O/0.1% TFA. Fractions containing pure product were collected, dissolved in MeOH, passed through a carbonate cartridge, and concentrated under reduced pressure to provide (S)-N6-(2-(2,3-dihydro-[1,4]dioxino[2,3-b]pyridin-8-yl)propyl)-N2′-methyl-[4,5′-bipyrimidine]-2′,6-diamine (Compound 462): ESMS=380.39 (M+H); 1H NMR (300 MHz, methanol-d4) δ 8.75 (s, 2H), 8.47 (s, 1H), 7.65 (d, J=5.3 Hz, 1H), 6.94 (d, J=5.2 Hz, 1H), 6.76 (s, 1H), 4.46-4.34 (m, 2H), 4.32-4.19 (m, 2H), 3.59 (ddd, J=12.0, 11.5, 7.3 Hz, 3H), 2.99 (s, 3H), 1.32 (d, J=6.7 Hz, 3H).
  • 10
  • [ 904326-88-1 ]
  • [ 1616290-27-7 ]
  • [ 1616290-50-6 ]
YieldReaction ConditionsOperation in experiment
74% With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate In 1,4-dioxane at 100℃; for 1h; Inert atmosphere; 128 A solution of 4-[2-(benzyloxy)-4,6-dimethylpyridin-3-yl]methyl}-9-bromo-6-methyl-7-(propan-2-yloxy)-3,4-dihydro-1,4-benzoxazepin-5(2H)-one (116 g, 121 mg, 0.224 mmol), N-m ethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidin-2-amine (52.7 mg, 0.224 mmol) and sodium carbonate (2.0 M, 71.2 mg, 0.672 mmol) in 1,4-dioxane (2.0 mL) was degassed (N2) for 5 min, then PdCl2(dppf)-DCM (50.0 mg, 0.0610 mmol) was added. The reaction was heated at 100° C. for 1 hour. The reaction was diluted with water (25 mL) and EtOAc (25 mL). The layers were separated and the organic phase was dried with magnesium sulfate and concentrated under vacuum. The residue was purified by column chromatography (silica gel, heptanes/EtOAc) to give 4-[2-(benzyloxy)-4,6-dimethylpyridin-3-yl]methyl}-6-methyl-9-[2-(methylamino)pyrimidin-5-yl]-7-(propan-2-yloxy)-3,4-dihydro-1,4-benzoxazepin-5(2H)-one (128a, 94 mg, 74% yield) as a white solid.
  • 11
  • [ 904326-88-1 ]
  • N-(4-bromo-3-[(dimethylamino)methylidene]sulfamoyl}phenyl)-2-(2-chlorophenyl)acetamide [ No CAS ]
  • 2-(2-chlorophenyl)-N-(3-[(dimethylamino)methylidene]sulfamoyl}-4-[2-(methylamino)pyrimidin-5-yl]phenyl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium fluoride; bis(triphenylphosphine)palladium(II) dichloride; triphenylphosphine In propan-1-ol; water at 100℃; for 1h; Inert atmosphere; 301 2-(2-Chlorophenyl)-N-{4-[2-(methylamino)pyrimidin-5-yl]-3- sulfamoylphenyl}acetamide N-(4-Bromo-3-[(dimethylamino)methylidene]sulfamoyl}phenyl)-2-(2-chlorophenyl)-acetamide (250 mg, 545 pmol) and N-methyl-5-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2- yl)pyrimidin-2-amine (256 mg, 1.1 mmol) were dissolved in n-propanol (8.1 ml) and bis(triphenylphosphine)palladium(l I) dichloride (CAS 13965-03-2) (19.2 mg, 27.2 pmol), triphenylphosphine (5.4 p1, 27 pmol), potassium fluoride (7.91 mg, 136 pmol) and aqueouspotassium phosphate (540 p1, 2.0 M, 1.1 mmol) were added. The solution was purged with argon for 5 minutes and the reaction was heated at 100°C for lh in the microwave. Afterwards the mixture was filtered over Celite, the solvent was removed under reduced pressure and the crude was used without further purification in the next step.
  • 12
  • [ 904326-88-1 ]
  • (R)-3-bromo-5-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)pyridine [ No CAS ]
  • (R)-5-(5-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)pyridin-3-yl)-N-methylpyrimidin-2-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
28% With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In 1,4-dioxane at 90℃; for 2h; Inert atmosphere; 45 4.1.15 3-((2,4-dichlorobenzyl)oxy)-5-(5-(piperidin-1-ylmethyl)thiophen-2-yl)pyridine (15) General procedure: A reaction solution of 3-bromo-5-((2,4-dichlorobenzyl)oxy)pyridine (12a) (150.00mg, 0.45mmol) and 1-((5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiophen-2-yl)methyl)piperidine (13c) (138.27mg, 0.45mmol) in 1,4-dioxane (15.00mL) was purged with nitrogen. Then PdCl2(PPh3)2 (15.44mg, 0.022mmol) and 1.0M of Na2CO3 (143.08mg, 1.35mmol) aqueous solution were added. The resulting mixture was purged with nitrogen and stirred at 90°C for 2h. The reaction mixture was filtered through a Celite pad and washed well with MeOH. The residue was partitioned between DCM and saturated aqueous NaHCO3 solution and brine. The organic layer was dried over MgSO4 and concentrated in vacuo and the resulting crude mixture was purified by a silica gel column, eluting with EA:Hexane (1:1) to collect the title product (15) as a yellow solid (116.00mg, 59%)
  • 13
  • [ 904326-88-1 ]
  • (S)-3-bromo-5-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)pyridine [ No CAS ]
  • (S)-5-(5-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)pyridin-3-yl)-N-methylpyrimidin-2-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
6% With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; caesium carbonate In 1,2-dimethoxyethane at 90℃; for 2h; Inert atmosphere; 49 4.1.14 3-((2,4-dichlorobenzyl)oxy)-5-(thiophen-2-yl)pyridine (14) General procedure: A reaction solution of 3-bromo-5-((2,4-dichlorobenzyl)oxy)pyridine (12a) (120.00mg, 0.36mmol) and 4,4,5,5-tetramethyl-2-(thiophen-2-yl)-1,3,2-dioxaborolane (13b) (75.64mg, 0.36mmol) in DME (15.00mL) was purged with nitrogen. Then Pd (dppf)Cl2CH2Cl2 (12.53mg, 0.015mmol) and 1.0M of Cs2CO3 (351.89mg, 1.08mmol) aqueous solution were added. The resulting mixture was purged with nitrogen and stirred at 90°C for 2h. The reaction mixture was filtered through a Celite pad and washed well with MeOH. The residue was partitioned between DCM and saturated aqueous NaHCO3 solution and brine. The organic layer was dried over MgSO4 and concentrated in vacuo and the resulting crude mixture was purified by a silica gel column, eluting with EA:Hexane (1:1) to collect the title product (14) as a white solid (72.00mg, 36%);
  • 14
  • [ 904326-88-1 ]
  • tert-butyl N-[3-chloro-6-fluoro-4-[3-(trifluoromethyl)pyrazol-1-yl]-9H-pyrido[2,3-b]indol-8-yl]-N-ethylcarbamate [ No CAS ]
  • C27H26F4N8O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0); XPhos In 1,4-dioxane; water at 100℃; for 12h; Inert atmosphere;
  • 15
  • [ 904326-88-1 ]
  • 3-(p-bromophenyl)-5-hydroxy-5-trifluoromethyl-Δ2-isoxazoline [ No CAS ]
  • 3-{4-[2-(methylamino)pyrimidin-5-yl]phenyl}-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-5-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
39% With dichloro[1,1'-bis(di-t-butylphosphino)ferrocene]palladium(II); caesium carbonate In 1,4-dioxane; water at 85℃; for 1h; 3-{4-[2-(Methylamino)pyrimidin-5-yl]phenyl)-5-(trifluoromethyl)-4,5-dihydro-1 ,2-oxazol-5-ol (compound I-001) To N-methyl-5-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)pyrimidin-2-amine (83 mg, 0.35 mmol) and [1 ,1 -Bis(di-tert-butylphosphino)ferrocene]dichloropalladium (II) (10 mg, 0.016 mmol) were added a solution of cesium carbonate (1 15 mg, 0.35 mmol) in water (0.8 ml) and a solution of 3-(4-bromophenyl)- 5-(trifluoromethyl)-4,5-dihydro-1 ,2-oxazol-5-ol (100 mg, 0.32 mmol) in dioxane (2.4 ml). The mixture was stirred at 85°C for 1 h and then cooled to rt. The reaction mixture was then concentrated and diluted with dichloromethane. The suspension was given onto a 2g silica cartridge, eluted with dichloromethane and evaporated. The residue was purified using preparative HPLC-MS (SunFire Waters, 30*150, 5 pm, eluent: acetonitrile/water (0.1 % formic acid)) to afford the title compound (43 mg, 39% yield). MS (ESI): 339 ([M+H]+)
Historical Records

Related Functional Groups of
[ 904326-88-1 ]

Organoboron

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Organoboron

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Esters

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Related Parent Nucleus of
[ 904326-88-1 ]

Pyrimidines

Chemical Structure| 1032759-30-0

[ 1032759-30-0 ]

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